3-Bromo-4-fluorobenzotrifluoride → 1,3,2-Dioxaborolane, 2-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-

HRID 1490556Notes

Reaction equation

HRID 1490556 reaction equation
Fc1ccc(C(F)(F)F)cc1Br>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CC1(C)OB(c2cc(C(F)(F)F)cc(Br)c2F)OC1(C)C

Participants

6

Reactant 1

HCID 1442953-Bromo-4-fluorobenzotrifluoride

Product 1

HCID 1223808011,3,2-Dioxaborolane, 2-[3-bromo-2-fluoro-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-Yield 100%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

The general procedure A was followed using 2-bromo-1-fluoro-4-(trifluoromethyl)benzene (71.5 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5l was obtained as white solid (185.2 mg, 100%) after purification by silica gel flash chromatography (EtOAc/PE= 1:20 v/v). m.p.: 70-72 oC.

Sources & evidence

ORD record
ord-93c3c6b491e44d96965f16d499773527
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…